2-Chloroadenosine → 2-Thioadenosine

HRID 917837

Reaction equation

HRID 917837 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[SH2:21].[Na]>CN(C)C=O>[CH:7]1[N:8]([C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[C:18]2[C:5](=[C:4]([NH2:20])[NH:3][C:2]([N:19]=2)=[S:21])[N:6]=1

Participants

4

Reactant 2

HCID 89742-ChloroadenosineHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 64519652-ThioadenosineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The starting material, the 2-thioadenosine of the formula (IV), used in the above Process 2 can be obtained in high yield from 2-chloroadenosine of the formula (II) by the procedure disclosed in Japanese Patent Application OPI No. 52,795/1973. That is, 2-chloroadenosine is reacted with sodium hydrogen sulfide in a solvent such as dimethylformamide at a temperature of about 50°C to 100°C to obtain the desired 2-thioadenosine of the formula (IV) in about 100% yield. The preparation of the starting material of the formula (IV) will be hereinafter described in greater detail in Reference Example 2.

Sources & evidence

ORD record
ord-c4bf991a73df41749e41cb2ca6be71d4
Source dataset
uspto-grants-1976_07
Patent number
US03968102

Linked notes

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